Water → HCID 86598318, compound

HRID 1393373Notes

Reaction equation

HRID 1393373 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:11][O:12][C:13](=[O:36])[C@H:14]([CH2:22][C:23]1[CH:28]=[C:27]([Cl:29])[C:26]([O:30][CH2:31][CH2:32][CH2:33][NH2:34])=[C:25]([Cl:35])[CH:24]=1)[NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18].C(=O)(O)[O-].[Na+].O>C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:36])[C@H:14]([CH2:22][C:23]1[CH:24]=[C:25]([Cl:35])[C:26]([O:30][CH2:31][CH2:32][CH2:33][NH:34][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:27]([Cl:29])[CH:28]=1)[NH:15][C:16](=[O:21])[C:17]([F:20])([F:18])[F:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 86598315HCID 86598315, compound

Product 1

HCID 86598318HCID 86598318, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

A solution of benzoyl chloride (94 mg, 0.669 mmol) in ethyl acetate (2 ml) was added dropwise to a two-layer solution of O-(3-aminopropyl)-3,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester hydrochloride (209 mg, 0.461 mmol) and sodium bicarbonate (150 mg, 1.79 mmol) in ethyl acetate (3 ml)-water (2 ml) with stirring under ice cooling and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was diluted with ethyl acetate (20 ml) and the organic layer was separated, washed with brine and dried. The solvent was distilled off under reduced pressure. The residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=2−1) to give O-(3-benzoylaminopropyl)-3,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester (253 mg, 100%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hr
  2. customthe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=2−1)

Sources & evidence

ORD record
ord-b88cd99168e547a79d9bdbcb3e29a9af
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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